期刊
CHEMICAL & PHARMACEUTICAL BULLETIN
卷 66, 期 3, 页码 231-234出版社
PHARMACEUTICAL SOC JAPAN
DOI: 10.1248/cpb.c17-00545
关键词
carboxylic acid; aldol reaction; boron catalyst; trifluoromethyl ketone
资金
- Japan Society for the Promotion of Science (JSPS)
- JSPS
- TORAY Award in Synthetic Organic Chemistry, Japan
- Grants-in-Aid for Scientific Research [17K19479, 15K07851, 17H06442] Funding Source: KAKEN
A catalytic carboxylic acid-selective aldol reaction with trifluoromethyl ketones was developed. Reversible and selective covalent bond formation between a boron catalyst and a carboxylic acid is key to realizing the unprecedented catalytic aldol reaction of simple carboxylic acids. The reaction proceeded chemoselectively at the a-position of carboxylic acid even in the presence of ketone, ester, or amide functional groups in the donor substrates. The chemoselectivity is beneficial for late-stage derivatizations of biologically relevant compounds, as demonstrated by the conversion of indomethacin and triacetylcholic acid.
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